May 30, 2014

For the last 10 years, I’ve been a professional dating coach with Love Systems. I help men succeed with women, from meeting and attracting women at bars and coffee shops straight through relationships and even breakups.

One thing I’ve noticed across over 10,000 clients is that dates are actually the worst place to screw things up. If you mess up when you first approach a woman, you’ve lost 15 seconds and maybe bruised your ego. If things don’t go well on a date, you’ve lost the time and money from the date itself, from the first time you met her, and all of the phoning and texting in between. Fail early, not late. To that end, I’d like to share these nine dumb things not to do on a first date. These tips won’t get you the girl on their own, but they’ll stop you from sinking your own ship unnecessarily.

Dumb First Date Move #1 – Expect her to pay

The biggest rule with money and dating is to never let money cause awkwardness. Don’t look at money as a tool in your arsenal. Think of it as a bomb you don’t want to go off.

For example, most women will expect you to pay for at least most of the first date. In an age of equal-pay laws, you can be political about this, but what’s the point? Plenty of things in our world are illogical, and you’re not going to get much sympathy talking about how men get a rough deal in society. Assume you’re paying.

Now, some women will resent the notion that they need to be paid for on the first date. So if she insists on splitting the bill or paying for some activity even after you’ve declined her offer once, then let her. It’s that simple.

Dumb First Date Move #2 – Take her somewhere super expensive

This is a more subtle flaw than expecting her to pay, but it can be just as devastating.

A lot of women will be turned off by an overly-expensive first date. They will be anxious that you will “expect something” at the end of the night for what you spent. Or they will wonder if you have so little going for you that you essentially have to try to buy affection.

Even if she’s not turned off, overspending can be counter-productive. A friend of my ex-girlfriend was being pursued by a rich businessman from Hawaii. He flew her around, bought her jewelry, and spared no expense. I asked her how he was in bed. Her response: “Are you kidding? I’m not going to sleep with him. if he’s spending this much to pursue me, I’m going to keep the chase going as long as I can.”

Dumb First Date Move #3 – Overinvesting

The Dumb First Date Move #2 was overinvesting financially, and #3 is overinvesting in any other way. When I was in college, long before Love Systems, I invited a woman to my place for dinner. I cooked a delicious meal from scratch and organized my apartment to be lit entirely by over 200 candles. It looked beautiful. It was romantic.

And it was a complete failure.

Overinvesting on the first date sends the same kind of signals as telling a woman you just met what an amazing person she is. It makes most women uncomfortable, because she knows she hasn’t earned the value you are placing on her yet. So your affection isn’t about her – it’s desperation, or a mechanical desire to be with any attractive woman you see. Neither point of view is attractive to most women.

Dumb First Date Move #4 - Grill her

Don’t bombard her with questions. So many men do this, and I’ve heard lots of women compare the process to “interviewing for a job that I don’t even know if I want.” No one goes to job interviews for fun.

But isn’t the point of a first date to get to know each other? Yes – but getting to know each other is as much about chemistry and emotional fit as it is about comparing facts about each other’s lives.

Of course, you’ll want to ask some questions – and you should. But questions aren’t the only way to get information. If you tell her something about yourself, she’ll probably reciprocate with the same information. Or use statements or even guesses. Instead of asking her what she studied in college, take a guess. Instead of asking her how she felt on her canoe trip, tell her it sounds very fun and peaceful. And so on.

Dumb First Date Move #5 – Dinner and a movie

This one won’t completely kill you, but it’s really not ideal. Dinner-and-a-movie dates are very conventional and will remind her of every other first date she’s been on instead of revealing your uniqueness.

Both parts of a dinner-movie night are bad for first dates. First date dinners can be awkward--you can’t touch, and there’s little external source of entertainment. Movies provide almost no opportunity to get to know each other.

Instead, take her somewhere more fun and interactive, like a comedy club or bowling alley. You can talk, touch, have fun, and be entertained. And she’ll probably love you for it.

Dumb First Date Move #6 – Argue about facts or logic

It’s okay to disagree with her. In fact, it’s good to do so a couple times, to show her that you’re your own man and not hung up on someone’s approval. But this is best done over subjective topics, where there is no right answer. She says he likes oranges; I say oranges are disgusting and apples are the bomb. And keep it playful.

What you don’t want to do is argue about whether global warming is real, or who invented the telescope. Even if you know she’s wrong, even if you can prove she’s wrong by browsing your phone, even if it’s completely common sense, let it go. If you see her again and develop something with her, there will be plenty of time to show her the truth later.

Dumb First Date Move #7 - Brag about yourself

You absolutely want her to know about your best qualities. But you want to communicate them to her in a way that she finds interesting and compelling, not braggy or insecure.

It’s natural to talk about yourself – or blurt out anything – when you’re nervous or feel an awkward pause in the conversation (another reason to avoid dinner and a movie). But it’s OK on dates to let a silence develop and let her fill it once in a while. It’s not like at a bar, where she could wander off any moment and you need to keep the energy level high at least for the first few minutes.

You’re best off revealing your good qualities through a Love Systems technique called embedding. Tell a story about something you’d tell anyway, but fit in ‘incidental’ details for her to ‘discover’ about you.

For example, you could tell a funny story of something that happened at a restaurant, mentioning in passing this took place during you last trip to China. If the “China” angle is purely incidental, the reference will seem incidental. In doing so, you’ve conveyed that you’re a traveler and must have at least a certain amount going for you. For more on this, there’s a great Love Systems article (with examples) about how to tell stories to meet women.

Dumb First Date Move #8 – Being negative

You’ve probably heard by now not to be negative about your ex-girlfriend, and that’s good advice. But it’s even better not to be negative in general. People who are negative about their family, friends, career, etc., usually aren’t very happy people or much fun to be around.

Just as importantly, guys who complain about everything don’t generally have very good lives. Instead of believing that everyone in your life has randomly done you wrong, she might reason that the common element in all of your complaints is you.

Be positive. It’s easy to do and will make a big difference.

Dumb First Date Move #9 – Making a second date

This might seem paradoxical. Presumably, if you are attracted to each other, you want a second date. That’s true, but you still don’t want to make the second date during the first.

Flirting and romantic tension is part of the process for a lot of women, and if she knows that she’s earned a second date already, that deprives her of wondering when you’re going to text or call to invite her out again. You won’t come across as much of a challenge – and, as I wrote in my book The Magic Bullets Handbook, being a challenge is one of the eight crucial factors to attract beautiful women. Press too quickly for a second date and she might start to doubt her attraction to you.

A partial exception – you can make vague long-term plans during any date as long they’re not specific – e.g., “You like sushi too? Awesome, we should go to that new place on the beach sometime this summer." Just don’t get specific or make firm plans.